Keith Hefner, the brother and “best friend” of Playboy owner Hugh Hefner, died Friday morning in his California home to causes not yet announced, just a day before his brother’s 90th birthday. Keith was 87 and frequent featured on E!’s The Girls Next Door. He had been battling with cancer and had been spotted looking frail in the days leading up to his death. Although his illness did not affect his spirit, as he was seen just last Tuesday on Snapchat, enjoying time with his wife, a Playboy model, Caya Ukkas.

In addition to his appearances on Girls Next Door, Keith was a longtime executive at Playboy Enterprises. He helped train and recruit models for the publication. When he was younger he dabbled in acting, with appearing on two episodes of Get Smart in 1969 and the films Evil Town (1977) and Fever Pitch (1985).

Hugh expressed his grief on Twitter:

His Girls Next Door costar also wrote:

This comes just months after Playboy Mansion was officially listed on the market for $200 million.

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